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  • Article
  • Open Access
12 Citations
8,185 Views
10 Pages

Cross-Coupling Reaction with Lithium Methyltriolborate

  • Yasunori Yamamoto,
  • Kazuya Ikizakura,
  • Hajime Ito and
  • Norio Miyaura

28 December 2012

We newly developed lithium methyltriolborate as an air-stable white solid that is convenient to handle. The good performance of this triolborate for metal-catalyzed bond-forming reactions was demonstrated in palladium-catalyzed cross-coupling reactio...

  • Article
  • Open Access
3 Citations
4,875 Views
12 Pages

Highlights on the General Preference for Multi-Over Mono-Coupling in the Suzuki–Miyaura Reaction

  • Carlos F. R. A. C. Lima,
  • Marco A. L. Lima,
  • J. Ricardo M. Pinto,
  • M. Gabriela T. C. Ribeiro,
  • Artur M. S. Silva and
  • Luís M. N. B. F. Santos

24 May 2023

A systematic synthetic study was performed to explain the usual trend in selectivity towards multi-coupling, over mono-coupling, in Suzuki–Miyaura reactions. This preference was observed under different reaction conditions: for various halobenz...

  • Article
  • Open Access
3,977 Views
10 Pages

19 October 2023

Organotitanium compounds find application in diverse reactions, including carbon–carbon bond formation and oxidation. While titanium (IV) compounds have been used in various applications, the potential of bis(cyclopentadienyl)diaryltitanium in...

  • Article
  • Open Access
24 Citations
8,113 Views
17 Pages

24 November 2016

A highly efficient and stable Pd-diimine@SBA-15 catalyst was successfully prepared by immobilizing Pd onto diimine-functionalized mesoporous silica SBA-15. With the help of diimine functional groups grafted onto the SBA-15, Pd could be anchored on a...

  • Article
  • Open Access
8 Citations
8,245 Views
22 Pages

28 September 2010

A Lewis acid-mediated three-component coupling reaction was successfully applied for the synthesis of lasofoxifene (1), nafoxidine (2), and their positional isomers, inv-lasofoxifene (3) and inv-nafoxidine (4). In the presence of HfCl4, the desired o...

  • Article
  • Open Access
14 Citations
5,678 Views
15 Pages

Preparation of Synthetic and Natural Derivatives of Flavonoids Using Suzuki–Miyaura Cross-Coupling Reaction

  • Martina Hurtová,
  • David Biedermann,
  • Zuzana Osifová,
  • Josef Cvačka,
  • Kateřina Valentová and
  • Vladimír Křen

31 January 2022

Herein, we report the use of the Suzuki–Miyaura cross-coupling reaction for the preparation of a library of synthetic derivatives of flavonoids for biological activity assays. We have investigated the reactivity of halogenated flavonoids with a...

  • Article
  • Open Access
6 Citations
5,437 Views
11 Pages

22 April 2019

An efficient arylation of SEM-protected pyrroles by the Suzuki–Miyaura coupling reaction has been developed. The reaction can be carried out under mild conditions to provide aryl-substituted pyrroles in moderate to excellent yields. The scope a...

  • Article
  • Open Access
14 Citations
3,127 Views
8 Pages

Ag–ZnO Nanocomposites Are Used for SERS Substrates and Promote the Coupling Reaction of PATP

  • Liping Ma,
  • Qijia Zhang,
  • Jia Li,
  • Xuemei Lu,
  • Ce Gao,
  • Peng Song and
  • Lixin Xia

15 February 2021

Noble metal-semiconductor nanocomposites have received extensive attention in Surface Enhanced Raman Scattering (SERS) due to their unique properties. In this paper, the Ag–ZnO nanocomposites are prepared by hydrothermal growth and simple chemical re...

  • Article
  • Open Access
21 Citations
4,567 Views
10 Pages

Construction of Self-Healing Disulfide-Linked Silicone Elastomers by Thiol Oxidation Coupling Reaction

  • Yanhua Huang,
  • Jianpan Yan,
  • Dengxu Wang,
  • Shengyu Feng and
  • Chuanjian Zhou

28 October 2021

Developing self-healing silicone elastomers are highly significant because of their promising applications. Herein, we present novel self-healing disulfide-linked silicone elastomers (SEs) based on thiol-terminated sulfur-containing heterochain polys...

  • Article
  • Open Access
9 Citations
2,980 Views
11 Pages

Improving Photocatalytic Stille Coupling Reaction by CuPd Alloy-Doped Ordered Mesoporous TiO2

  • Ting Tang,
  • Lehong Jin,
  • Wei Chai,
  • Jing Shen,
  • Zhenmin Xu and
  • Haifang Mao

14 October 2022

Rational surface engineering of noble metal-doped photocatalysts is essential for the efficient conversion of solar energy into chemical energy, but it is still challenging to perform. Herein, we reported an effective strategy for structuring alloyed...

  • Article
  • Open Access
19 Citations
4,185 Views
10 Pages

Highly Crystallized Pd/Cu Nanoparticles on Activated Carbon: An Efficient Heterogeneous Catalyst for Sonogashira Cross-Coupling Reaction

  • Zhen Wei,
  • Zunyuan Xie,
  • Lingxiang Gao,
  • Yanyan Wang,
  • Huaming Sun,
  • Yajun Jian,
  • Guofang Zhang,
  • Liwen Xu,
  • Jianming Yang and
  • Ziwei Gao
  • + 1 author

5 February 2020

In the quest for efficient and recyclable heterogeneous catalysts for Sonogashira coupling reactions, a PEG-OMe (Methoxy Polyene Glycol) - mediated method was developed to immobilize Pd/Cu bimetallic nanoparticles on activated carbon (AC). Catalytic...

  • Article
  • Open Access
20 Citations
6,343 Views
17 Pages

5 March 2012

MG 50-3-1 (3, trisodium 1-amino-4-{4-[4-chloro-6-(2-sulfophenylamino)-1,3,5-triazin-2-ylamino]-2-sulfophenylamino}-9,10-dioxo-9,10-dihydroanthracene 2-sulfonate) is the most potent and selective antagonist (IC50 4.6 nM) for “P2Y1-like” nucleotide-act...

  • Article
  • Open Access
5 Citations
5,088 Views
8 Pages

1 August 2020

C–C bond formation is one of the most important implements in synthetic organic chemistry. In pursuit of effective synthetic routes functioning under greener pathways to achieve direct C–C bond formation, we report N-iodosuccinimide (NIS)...

  • Article
  • Open Access

Photocatalytic Phenylmethylamine Coupling Reaction of Organic–Inorganic Composites Based on Benzothiophene Polymers and TiO2

  • Xin Li,
  • Zhaozheng Yang,
  • Lingyu Tai,
  • Chengzhi Ma,
  • Yuqing Hu,
  • Jiawei Cai,
  • Xin Shen,
  • Pinghuai Liu,
  • Lilin Tan and
  • Yifan Chen

19 March 2026

Benzothiophene polymers, as a class of novel organic semiconductor materials, exhibit significant potential in the field of photocatalysis due to their broad light-responsive range and tunable energy level structures. In this study, a benzothiophene-...

  • Article
  • Open Access
8 Citations
6,613 Views
8 Pages

5 September 2016

An efficient PdII/Pd0-p-benzoquinone/hydroquinone-CuCl2/CuCl catalyst system was developed that uses environmentally friendly molecular oxygen as the terminal oxidant to catalyze the cyclization-carbonylation-cyclization coupling reaction (CCC-coupli...

  • Article
  • Open Access
8 Citations
6,021 Views
20 Pages

20 July 2020

Several methods to synthesize poly(phenylene) block copolymers through the nickel coupling reaction were attempted to reduce the use of expensive nickel catalysts in polymerization. The model reaction for poly(phenylene) having different types of dic...

  • Article
  • Open Access
1 Citations
2,692 Views
11 Pages

20 June 2023

The synthesis of efficient and sustainable heterogeneous Pd-based catalysts has been an active field of research due to their crucial role in carbon–carbon coupling reactions. In this study, we developed a facile and eco-friendly in situ assembly tec...

  • Article
  • Open Access
35 Citations
4,527 Views
14 Pages

Pd Nanocatalyst Adorned on Magnetic Chitosan@N-Heterocyclic Carbene: Eco-Compatible Suzuki Cross-Coupling Reaction

  • Roya Sedghi,
  • Bahareh Heidari,
  • Hatef Shahmohamadi,
  • Pourya Zarshenas and
  • Rajender S. Varma

22 August 2019

A novel magnetic-functionalized-multi-walled carbon nanotubes@chitosan N-heterocyclic carbene-palladium (M-f-MWCNTs@chitosan-NHC-Pd) nanocatalyst is developed in two steps. The first step entails the fabrication of a three-component cross-linking of...

  • Article
  • Open Access
25 Citations
8,598 Views
13 Pages

Diazotization-Coupling Reaction-Based Determination of Tyrosine in Urine Using Ag Nanocubes by Surface-Enhanced Raman Spectroscopy

  • Yudong Lu,
  • Dechan Lu,
  • Ruiyun You,
  • Jialing Liu,
  • Luqiang Huang,
  • Jingqian Su and
  • Shangyuan Feng

A novel, simple, and highly sensitive method was developed to detect the concentration of tyrosine-derived azo dye indirectly using silver nanocubes (AgNCs) as a substrate on a super-hydrophobic silver film by surface-enhanced Raman spectroscopy (SER...

  • Article
  • Open Access
7 Citations
3,819 Views
13 Pages

5 July 2021

A new series of xylyl-linked bis-benzimidazolium salts were efficiently prepared using a simple preparation method from bis-benzimidazolium precursors featuring highly tunable linkers and wingtips. A highly efficient Suzuki–Miyaura cross-coupling rea...

  • Article
  • Open Access
3 Citations
1,872 Views
15 Pages

Eco-Friendly Cellulose-Supported Nickel Complex as an Efficient and Recyclable Heterogeneous Catalyst for Suzuki Cross-Coupling Reaction

  • Zhanyu Li,
  • Guohao Zhou,
  • Yu Sun,
  • Yingning Mao,
  • Fanxiang Zeng,
  • Zhihui Wang,
  • Yuanyuan Zhang and
  • Bin Li

24 September 2024

In this work, we applied commercially available 2-pyridinecarboxylic acid to modify cellulose by simple manipulations, and then anchored low-toxicity metal nickel onto the modified cellulose to prepare the heterogeneous catalyst (CL-AcPy-Ni). The obt...

  • Article
  • Open Access
1,730 Views
21 Pages

1 February 2025

The application of metal–organic frameworks (MOFs) has attracted increasing attention in organic synthesis. The modification of MOFs can efficiently tailor the structure and improve the property for meeting ongoing demand in various application...

  • Article
  • Open Access
1,450 Views
11 Pages

29 January 2025

There is relatively little research on cyclic amphiphilic block polymers, having both hydrophilic and hydrophobic segments placed in the ring and thus resulting in a higher degree of topological restriction, as drug vehicles. Cyclic amphiphilic binar...

  • Article
  • Open Access
13 Citations
3,405 Views
13 Pages

7 January 2021

Artificial sensory substitution systems can mimic human sensory organs through replacing the sensing process of a defective sensory receptor and transmitting the sensing signal into the nervous system. Here, we report a self-powered flexible gustatio...

  • Article
  • Open Access
10 Citations
3,654 Views
18 Pages

Facile Green Preparation of Rhodium Nanoclusters Supported Nano-Scaled Graphene Platelets for Sonogashira Coupling Reaction and Reduction of p-Nitrophenol

  • Gopiraman Mayakrishnan,
  • Saravanamoorthy Somasundaram,
  • Sana Ullah,
  • Ilangovan Andivelu,
  • Kim Ick Soo and
  • Chung Ill Min

30 October 2019

Rhodium nanoclusters were uniformly dispersed on nano-scaled graphene platelets by a simple ‘mix and heat’ method without using any toxic reagents. Distilled water was used to obtain the homogenous dispersion of Rh-nanoclusters on graphen...

  • Article
  • Open Access
14 Citations
5,260 Views
13 Pages

17 October 2018

Plasmonic nanostructures can be employed for performing photocatalytic reactions with visible-light illumination involving two different possible mechanisms, namely, the near-field enhancement and/or direct hot-electron transfer to the conduction ban...

  • Review
  • Open Access
237 Citations
20,579 Views
22 Pages

31 July 2020

Cross-coupling reactions have played a critical role enabling the rapid expansion of structure–activity relationships (SAR) during the drug discovery phase to identify a clinical candidate and facilitate subsequent drug development processes. T...

  • Article
  • Open Access
2 Citations
2,262 Views
12 Pages

N-Heterocyclic Carbene Silver Complex Modified Polyacrylonitrile Fiber/MIL-101(Cr) Composite as Efficient Chiral Catalyst for Three-Component Coupling Reaction

  • Ningning Xin,
  • Xuemin Jing,
  • Cheng-Gen Zhang,
  • Xiaoxia Peng,
  • Jing Liu,
  • Qixing Wang,
  • Wei Wang,
  • Jian Cao and
  • Minli Tao

24 November 2022

Complex asymmetric synthesis can be realized by the chiral induction of amino acids in nature. It is of great significance to design a new biomimetic catalytic system for asymmetric synthesis. In this context, we report the preparation and characteri...

  • Article
  • Open Access
1,087 Views
13 Pages

10 June 2025

Na-layered Li-containing Mn-based cathodes (NaxLiyMn1-yO2, NLMOs) with additional Na+ storage ability resulting from the anionic redox reaction (ARR) hold great promise for sodium-ion batteries (NIBs). However, practical applications of NLMOs encount...

  • Article
  • Open Access
6 Citations
3,421 Views
24 Pages

4 October 2024

Pyrazolo[3,4-b]pyridine scaffolds have been heavily exploited in the development of nitrogen-containing heterocycles with numerous therapeutic applications in the field of medicinal and pharmaceutical chemistry. The present work describes the synthes...

  • Review
  • Open Access
163 Citations
14,364 Views
15 Pages

25 March 2010

Since metal nanoparticles have a high surface-to-volume ratio and very active surface atoms, they are very attractive catalysts for a wide variety of organic and inorganic reactions, compared to bulk catalysts. Metal nanoparticles suspended in colloi...

  • Article
  • Open Access
25 Citations
18,681 Views
19 Pages

Efficient Synthesis of Novel Pyridine-Based Derivatives via Suzuki Cross-Coupling Reaction of Commercially Available 5-Bromo-2-methylpyridin-3-amine: Quantum Mechanical Investigations and Biological Activities

  • Gulraiz Ahmad,
  • Nasir Rasool,
  • Hafiz Mansoor Ikram,
  • Samreen Gul Khan,
  • Tariq Mahmood,
  • Khurshid Ayub,
  • Muhammad Zubair,
  • Eman Al-Zahrani,
  • Usman Ali Rana and
  • Noorjahan Banu Alitheen
  • + 1 author

27 January 2017

The present study describes palladium-catalyzed one pot Suzuki cross-coupling reaction to synthesize a series of novel pyridine derivatives 2a2i, 4a4i. In brief, Suzuki cross-coupling reaction of 5-bromo-2-methylpyridin-3-amine (1) directly or via...

  • Article
  • Open Access
19 Citations
5,842 Views
18 Pages

Ultrasound-Assisted Hydrazine Reduction Method for the Preparation of Nickel Nanoparticles, Physicochemical Characterization and Catalytic Application in Suzuki-Miyaura Cross-Coupling Reaction

  • Adél Anna Ádám,
  • Márton Szabados,
  • Gábor Varga,
  • Ádám Papp,
  • Katalin Musza,
  • Zoltán Kónya,
  • Ákos Kukovecz,
  • Pál Sipos and
  • István Pálinkó

28 March 2020

In the experimental work leading to this contribution, the parameters of the ultrasound treatment (temperature, output power, emission periodicity) were varied to learn about the effects of the sonication on the crystallization of Ni nanoparticles du...

  • Article
  • Open Access
15 Citations
6,591 Views
17 Pages

A Palladium Catalyst System for the Efficient Cross-Coupling Reaction of Aryl Bromides and Chlorides with Phenylboronic Acid: Synthesis and Biological Activity Evaluation

  • Boubakri Lamia,
  • Ahlem Chakchouk-Mtibaa,
  • Bilel Hallouma,
  • Lamjed Mansour,
  • Lotfi Mellouli,
  • Ismail Özdemir,
  • Sedat Yaşar and
  • Naceur Hamdi

New benzimidazolium salts 1a–c and their palladium bis-N-heterocyclic carbene complexes 2a–c and palladium PEPPSI-type complexes 3a–c were designed, synthesized and structurally characterized by NMR (1H and 13C), IR, DART-TOF mass spectrometry and el...

  • Feature Paper
  • Review
  • Open Access
36 Citations
8,083 Views
40 Pages

24 September 2020

Catalysis of cross-coupling reactions under phosphane-free conditions represents an important ongoing challenge. Although transition metal complexes based on the thiosemicarbazone unit have been known for a very long time, their use in homogeneous ca...

  • Article
  • Open Access
18 Citations
9,463 Views
15 Pages

Investigation of the Pyridinium Ylide—Alkyne Cycloaddition as a Fluorogenic Coupling Reaction

  • Simon Bonte,
  • Ioana Otilia Ghinea,
  • Rodica Dinica,
  • Isabelle Baussanne and
  • Martine Demeunynck

The cycloaddition of pyridinium ylides with alkynes was investigated under mild conditions. A series of 13 pyridinium salts was prepared by alkylation of 4-substituted pyridines. Their reactivity with propiolic ester or amide in various reaction cond...

  • Feature Paper
  • Article
  • Open Access
1,324 Views
21 Pages

Synergy in Sonogashira Cross-Coupling Reactions with a Magnetic Janus-Type Catalyst

  • Majid Vafaeezadeh,
  • Fatemeh Rajabi,
  • Xuanya Qiu,
  • Marco A. M. Tummeley,
  • Paul Hausbrandt,
  • Sven Schaefer,
  • Alina Ouissa,
  • Anna Demchenko,
  • Johannes L’huillier and
  • Werner R. Thiel
  • + 2 authors

1 December 2025

This work describes the straightforward synthesis of a novel heterogeneous palladium catalyst immobilized on magnetic Janus-type silica particles coated with an amphiphilic ionic liquid (IL) layer. The material was prepared via a one-pot process wher...

  • Feature Paper
  • Review
  • Open Access
45 Citations
9,020 Views
32 Pages

24 November 2020

The ever-growing interest in the cross-coupling reaction and its applications has increased exponentially in the last decade, owing to its efficiency and effectiveness. Transition metal-mediated cross-couplings reactions, such as Suzuki–Miyaura...

  • Review
  • Open Access
31 Citations
10,090 Views
35 Pages

31 December 2020

Cross-coupling reactions furnishing carbon–carbon (C–C) and carbon–heteroatom (C–X) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Ullmann, Ullman–Goldberg, Cadi...

  • Communication
  • Open Access
2 Citations
5,815 Views
24 Pages

Nickel-Catalyzed Kumada Cross-Coupling Reactions of Benzylic Sulfonamides

  • Kirsten A. Hewitt,
  • Claire A. Herbert,
  • Alissa C. Matus and
  • Elizabeth R. Jarvo

30 September 2021

Herein, we report a Kumada cross-coupling reaction of benzylic sulfonamides. The scope of the transformation includes acyclic and cyclic sulfonamide precursors that cleanly produce highly substituted acyclic fragments. Preliminary data are consistent...

  • Feature Paper
  • Article
  • Open Access
9 Citations
1,941 Views
14 Pages

In Situ Decorated Palladium Nanoparticles on Chitosan Beads as a Catalyst for Coupling Reactions

  • Khaoula Oudghiri,
  • Lahoucine Bahsis,
  • Said Eddarir,
  • Hafid Anane and
  • Moha Taourirte

3 August 2023

A green protocol for the in situ synthesis of Pd nanoparticles on chitosan beads (Pd NPs-CS) is reported without the need to use any toxic reducing agents. The preparation of the Pd nanoparticles catalyst was performed using a simple coordination rea...

  • Article
  • Open Access
5 Citations
4,490 Views
18 Pages

Insights into the Three-Component Coupling Reactions of Aldehydes, Alkynes, and Amines Catalyzed by N-heterocyclic Carbene Silver: A DFT Study

  • Chenggen Zhang,
  • Shuyuan Yu,
  • Fei Wang,
  • Jian Cao,
  • Xinru Liang,
  • Fuping Wang,
  • Huimin Zheng,
  • Yaning Zhang,
  • Mengyao Yang and
  • Boyu Zhao

23 March 2023

Density functional theory (DFT) was used to investigate the three-component coupling reactions of aldehydes, alkynes, and amines (A3 coupling) using N-heterocyclic carbene silver as the catalyst. This study reveals that the addition reaction between...

  • Review
  • Open Access
11 Citations
6,210 Views
30 Pages

22 January 2021

Plasmonic hybrid nanostructures have been investigated as attractive heterogeneous photocatalysts that can utilize sunlight to produce valuable chemicals. In particular, the efficient photoconversion of CO2 into a stable hydrocarbon with sunlight can...

  • Article
  • Open Access
1 Citations
5,411 Views
23 Pages

A Pd-catalyzed isomerization-coupling reaction of P-containing allyl chloride with amine afforded imine or enamine that was converted to various functionalized phosphorus derivatives via hydrolysis, reduction, or Stork reactions. The reaction was con...

  • Review
  • Open Access
32 Citations
11,889 Views
29 Pages

29 October 2014

Halogenated quinazolinones and quinazolines are versatile synthetic intermediates for the metal-catalyzed carbon–carbon bond formation reactions such as the Kumada, Stille, Negishi, Sonogashira, Suzuki-Miyaura and Heck cross-coupling reactions or c...

  • Review
  • Open Access
59 Citations
20,704 Views
35 Pages

18 December 2019

Cross-coupling reactions furnishing carbon–carbon (C–C) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Negishi, Heck, Kumada, Sonogashira, Stille, Suzuki, and Hiyama, utilizing pa...

  • Feature Paper
  • Review
  • Open Access
34 Citations
5,865 Views
60 Pages

4 October 2018

Carbon‒carbon (C‒C) and carbon‒heteroatom (C‒X) bonds that form via transition-metal-catalyzed processes have been extensively used in the organic synthesis and preparation of natural products and important compounds such as heterocycles, biologicall...

  • Article
  • Open Access
10 Citations
4,644 Views
20 Pages

Palladium-Catalyzed Mizoroki–Heck and Copper-Free Sonogashira Coupling Reactions in Water Using Thermoresponsive Polymer Micelles

  • Noriyuki Suzuki,
  • Shun Koyama,
  • Rina Koike,
  • Nozomu Ebara,
  • Rikito Arai,
  • Yuko Takeoka,
  • Masahiro Rikukawa and
  • Fu-Yu Tsai

13 August 2021

A few kinds of thermoresponsive diblock copolymers have been synthesized and utilized for palladium-catalyzed coupling reactions in water. Poly(N-isopropylacrylamide) (PNIPAAm) and poly(N,N-diethylacrylamide) (PDEAAm) are employed for thermoresponsiv...

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